methyl 2-O-(p-methoxybenzyl)-4,6-O-benzylidene-α-D-glucopyranoside | 214068-06-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2-O-(p-methoxybenzyl)-4,6-O-benzylidene-α-D-glucopyranoside
• 英文别名: (4aR,6S,7R,8S,8aS)-6-methoxy-7-[(4-methoxyphenyl)methoxy]-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 214068-06-1
• 化学式: C₂₂H₂₆O₇
• 分子量: 402.444
• InChiKey: VLEWSJLQKBHTFT-DNJZHPGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-O-(p-methoxybenzyl)-4,6-O-benzylidene-α-D-glucopyranoside 在 4-二甲氨基吡啶 、 sodium hydroxide 、 草酰氯 、 mercury(II) diacetate 、 氢气 、 四丁基碘化铵 、 三乙酰氧基硼氢化钠 、 sodium hydride 、 potassium carbonate 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 sodium chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 153.5h， 生成 (1S,2S,3R,4S,5S,6S)-4-Benzyloxy-2,6-bis-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol
  参考文献：
  名称：

  Synthesis of l-α-phosphatidyl-d-myo-inositol 5-phosphate and l-α-phosphatidyl-d-myo-inositol 3,5-bisphosphate

  摘要：

  Two new 5-phosphorylated phosphatidylinositols have been synthesized from methyl alpha-D-glucopyranoside as the chiral precursor. These new PtdInsP(n)s have been recently detected in mammalian cells. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00737-0
• 作为产物：
  描述：

  甲基-4,6-O-亚苄基-Α-D-吡喃葡糖苷 、 4-甲氧基氯苄 在 四丁基溴化铵 、 二正丁基氧化锡 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以36%的产率得到methyl 2-O-(p-methoxybenzyl)-4,6-O-benzylidene-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of l-α-phosphatidyl-d-myo-inositol 5-phosphate and l-α-phosphatidyl-d-myo-inositol 3,5-bisphosphate

  摘要：

  Two new 5-phosphorylated phosphatidylinositols have been synthesized from methyl alpha-D-glucopyranoside as the chiral precursor. These new PtdInsP(n)s have been recently detected in mammalian cells. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00737-0

文献信息

• Asymmetric Total Synthesis of Phosphatidylinositol 3-Phosphate and 4-Phosphate Derivatives
  作者：Jian Chen、Li Feng、Glenn D. Prestwich

  DOI：10.1021/jo980501r

  日期：1998.9.1

  New asymmetric syntheses of phosphatidylinositol 3-phosphate (PtdIns(3)P) and phosphatidylinositol 4-phosphate (PtdIns(4)P) derivatives are described. Key intermediates were used to prepare diacylglyceryl moieties with dibutyryl, dioctanoyl, and dihexadecanoyl chains. In addition, a modified route provided PtdIns(3)P and PtdIns(4)P triesters with P-1-linked aminopropyl groups for preparation of affinity probes. The synthesis of the inosityl precursor employed a dibutyltin oxide-mediated p-methoxybenzyl (PMB) etherification to give either the 2-PMB- or the 3-PMB-protected glucopyranosides. The Ferrier rearrangement was used to convert suitably protected glucose derivatives to enantiomerically pure, differentially protected D-myo-inositol key intermediates. A versatile phosphoramidite reagent was employed to allow synthesis of PtdInsP(n), derivatives with diacylglyceryl moieties of different chain lengths.
• Synthesis of l-α-phosphatidyl-d-myo-inositol 5-phosphate and l-α-phosphatidyl-d-myo-inositol 3,5-bisphosphate
  作者：Jirong Peng、Glenn D. Prestwich

  DOI：10.1016/s0040-4039(98)00737-0

  日期：1998.6

  Two new 5-phosphorylated phosphatidylinositols have been synthesized from methyl alpha-D-glucopyranoside as the chiral precursor. These new PtdInsP(n)s have been recently detected in mammalian cells. (C) 1998 Elsevier Science Ltd. All rights reserved.